I never have dealt well with “going” to work or “answering” to a boss. I know it sounds rather hopeless, but I have an entrepreneur-esque mind and I set out to never “go” to work or “answer” to anyone I didn’t want to answer to. And so far, I’ve achieved that goal.

I work 100% freelance. I make my own schedule. Some days I don’t work at all. I sleep in when I want to. I go out ’til 7 am if I want to. Hell, I take off to California if I want to. There are no rules, really, and many a friend have drooled their envy all over my face without taking a minute to really understand how NOT easy working for yourself can be. If you’re considering pursuing this lifestyle, but you’re not sure if it’s for you, maybe I can be of some help.

MOTIVATION

You’ve gotta be able to be self-motivated. You’ve got to make money and build your career REGARDLESS of the fact that there’s an X-Files marathon on channel 17.

ORGANIZATION

In this scenario, there is no boss around to tell you what you need to ‘do’ today. You have to be able to organize your thoughts and think for yourself. I personally make lonnnnnnng lists every single day. And I drink lots of caffeine.

TAXES MATTER

If you’re not keen on where and how to get tax breaks — then forget this lifestyle. You’ll never get away with it. Being a freelancer means being responsible for keeping your own taxes, writing off every relevant expense, and having excellent accounting skills. It’s tedious, but it matters.

DETERMINATION

Freelance jobs don’t last forever. You’ve gotta have enough determination to always be seeking out new work. People don’t always pay you, either. Can you get on the phone and call someone every single day who is stiffing you money? This crap happens and if it’s not in your personality to get down and dirty legally when you have to, then you should really STOP considering working freelance.

BENEFITS

You’re going to have to find ‘other’ ways to take care of your health. They DO exist, believe me. Freelancers Union, as well as many other organizations you may belong to (or could), do provide health care, and for relatively reasonable rates. You should also be able to research free medical services near you. I don’t believe that health benefits should keep a person in a job they don’t enjoy — but you’ve gotta apply yourself to get them otherwise.

My life DOES rock. I love making all of my own rules. But I love this scenario so much because it SUITS me. Does it REALLY suit you?